I've had good luck so far with the MityVac 7201 on the 4 vehicles in my fleet.
Here's an interesting youtube on extractors vs traditional plug draining:

 

He said he was going to show a comparison to using a extractor vs draining from the plug, but he didn't show how much oil was left after the extraction, so there was nothing to compare.

 

I think that was the part early on where he showed the pan with water in it and the plug removed Wayne.
I have the compressed air extractor he mentioned at the end, a Mitivac 7300, and I have used it on 3 different cars and the 722.6 transmission, as well as vacuum bleeding the brakes.
It does a fine job.

 

That looks like the one I bought at Northern Tool for about $20.

 

I bought the mighty vac 7201 through Amazon, about $90.00. It does the job but what's that old saying Grandma had, a watched kettle never boils? It takes at least a half-hour and even at 50 I get tired of waiting for it but it beats paying places like Firestone $180.
So giddy up. Back, Jack, do it again.

 

Just been draining into milk or ice tea jugs on a pair of ramps for most of my life. Gives me a chance to hit the lube points while there. Besides most of my cars have the oil filter reached from the bottom like was intended.